Tetrahydrofuran → 3-Bromo-7-iodothieno[3,2-c]pyridin-4(5H)-one

HRID 734314Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 734314
[Br:1][C:2]1[C:6]2[C:7](=[O:11])[NH:8][CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1.C1C(=O)N([I:19])C(=O)C1.C1COCC1.[O-]S([O-])=O.[Na+].[Na+]>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[C:6]2[C:7](=[O:11])[NH:8][CH:9]=[C:10]([I:19])[C:5]=2[S:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 24437Sodium SulfiteHCID 120273N-IodosuccinimideHCID 184507963-Bromothieno[3,2-c]pyridin-4(5H)-one

Produkt 1

HCID 578451273-Bromo-7-iodothieno[3,2-c]pyridin-4(5H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The mixture of compound 10 (see Example 4(c)) (1.9 g, 8.3 mmol) and N-iodosuccimide (NIS, 2.2 g, 49.9 mmol) in DMF (25 ml) and THF (20 ml) was stirred for 5 hours at 40° C. The reaction mixture was poured into 10% Na2SO3 and ethyl acetate. The insoluble product was collected by filtration, washed with ethyl acetate and dried under reduced pressure to give 3-bromo-7-iodo-5H-thieno[3,2-c]pyridin-4-one (990 mg). The filtrate was collected, dried over Na2SO4, filtered and concentrated in vacuo. The generated precipitate was washed with MeOH to further yield 3-bromo-7-iodo-5H-thieno[3,2-c]pyridin-4-one (1.1 g). 1H NMR (400 MHz, DMSO-d6) ppm 11.75 (s, 1H), 7.79 (s, 1H), 7.57 (s, 1H).

Aufarbeitung

  1. filtrationThe insoluble product was collected by filtration
  2. washwashed with ethyl acetate
  3. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1ca07353cebc4c92b0524f23949653c1
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592352B2

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